Hydrochloric Acid → 4-(6-Bromonaphth-2-ylsulphonyl)anisole

HRID 346674Notes

Reaction equation

HRID 346674 reaction equation
[Cl-].[Al+3].[Cl-].[Cl-].[Br:5][C:6]1[CH:7]=[C:8]2[C:13](=[CH:14][CH:15]=1)[CH:12]=[C:11]([S:16](Cl)(=[O:18])=[O:17])[CH:10]=[CH:9]2.[C:20]1([O:26][CH3:27])[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1.Cl>C(Cl)Cl.O>[Br:5][C:6]1[CH:7]=[C:8]2[C:13](=[CH:14][CH:15]=1)[CH:12]=[C:11]([S:16]([C:23]1[CH:24]=[CH:25][C:20]([O:26][CH3:27])=[CH:21][CH:22]=1)(=[O:18])=[O:17])[CH:10]=[CH:9]2

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 7519AnisoleHCID 6451240Aluminum(III) ChlorideHCID 144577416-Bromonaphthalene-2-sulfonyl chloride

Product 1

HCID 179157404-(6-Bromonaphth-2-ylsulphonyl)anisoleYield 23.1%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent2×

Conditions

Temperature
4 °C

Procedure

Aluminium chloride (3.33 g) was added portionwise over 30 minutes to a stirred mixture of 6-bromonaphth-2-ylsulphonyl chloride (6.11 g) and anisole (3.33 g) in dry methylene chloride (35 ml). The resultant mixture was stirred for 24 hours. Methylene chloride (75 ml) was added. the mixture cooled to 4° C. and water (100 ml) added cautiously. The mixture was acidified with 2M hydrochloric acid, separated and the aqueous phase extracted with methylene chloride (30 ml). The combined organic phases were washed with water, dried (MgSO4) and evaporated. Recrystallisation of the residue from an ethyl acetate/ethanol mixture gave 4-(6-bromonaphth-2-ylsulphonyl)anisole (1.74 g), m.p. 180-181° C.;

Workup

  1. customseparated
  2. extractionthe aqueous phase extracted with methylene chloride (30 ml)
  3. washThe combined organic phases were washed with water
  4. dry with materialdried (MgSO4)
  5. customevaporated
  6. customRecrystallisation of the residue from an ethyl acetate/ethanol mixture

Sources & evidence

ORD record
ord-0a6bb5cdc00a47d5b576e894b6d107ce
Source dataset
uspto-grants-2007_02
Patent number
US07173025B1

Reaction notes

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